ACE Organic Functional Groups

ORGANIC FUNCTIONAL GROUPS
Organic Functional Groups come up as tossups and, oftentimes, as bonus parts. Here are a few of the most commonly asked functional groups with brief descriptions of each. (Study Guide by Adam Silverman) Brief Description: The simplest organic functional groups are those of hydrocarbons, compounds which contain just hydrogen and carbon. These come in three types: alkanes, alkenes, and alkynes. Alkanes: Contain only single carbon-carbon bonds (C-C). Because of this, they are considered saturated with hydrogen. General formula: C n H 2n+2 Examples include methane, ethane, propane, and so on. Alkanes end in ane. Alkanes are generally unreactive. They can be formed by the hydrogenation of alkenes, or in the Wolff-Kishner Reduction of aldehydes/ketones. Alkenes: Have at least one double carbon-carbon bond (C=C). Alkenes end in ene. General formula: C n H 2n . Also known as olefins They are much more reactive than alkanes, formed in elimination reaction of alcohols or alkyl halides. In the Wittig Reaction, alkenes are formed from aldehydes and ketones. Alkynes: Have a carbon-carbon triple bond (CC). Their names end in yne, like ethyne and propyne. General formula: C n H 2n-2 . Alkynes can be hydrogenated to form alkenes. They are formed from aldehydes in the Corey-Fuchs reaction. Alcohols: Contain an oxygen atom bonded to hydrogen (O-H, or hydroxyl, group). Alcohols end in ol. Examples include methanol (CH 3 OH), ethanol (found in alcoholic beverages), and butanol.
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Alcohols participate in many reactions: they are oxidized into carboxylic acids and ketones, and they are dehydrated to form alkenes. Carbonyl Compounds: A carbonyl functional group consists of a carbon atom double bonded to an oxygen atom (C=O). These are present in two forms in organic compounds: aldehydes and ketones. Aldehydes: Have a terminal carbonyl group, meaning that the carbonyl is at the end of a carbon chain, or that the carbonyl carbon is bonded to hydrogen. The simplest aldehyde is formaldehyde (H 2 C=O). Other aldehydes end in al. When reacted with the Grignard reagent, aldehydes form tertiary alcohols. When mixed with the Tollens reagent, aldehydes form a silver mirror. Ketones: Have a non-terminal carbonyl group, with the carbonyl carbon occurring inside the carbon chain. The simplest ketone is acetone, (CH 3 ) 2 C=O. Ketones do not react with the Tollens reagent. They can be formed by the oxidation of secondary alcohols. Carboxylic Acids: Consist of a carbon double bonded to oxygen and single bonded to a hydroxyl (-OH) group. The carboxyl group is usually written COOH. Per their name, carboxylic acids are acidic; examples include acetic acid (CH 3 COOH). The simplest carboxylic acid is formic acid, HCOOH, which is found in ant venom. They are formed from aldehydes in the Cannizzaro Reaction. Esters: Contain a carbon double bonded to one oxygen, and single bonded to another (a carbonyl group bonded to oxygen). Formula: R-COO-R Esters smell fruity. Esters are commonly formed in the Fischer esterification, from treating a carboxylic acid with an alcohol. They also are used in the Claisen condensation. Other Functional Groups Ethers: Contain an oxygen atom that is bonded to two carbon atoms (R-O-R). Ethers were originally used as anesthetics, particularly the dimethyl ether (CH 3 OCH 3 ).
Ethers are formed in the Williamson Synthesis from alkyl halides and alcohols. Amines, Amides, and Nitriles: There are several nitrogen-containing function groups, but the most commonly encountered at the high school level are amines, amides, and nitriles. Amines consist of a nitrogen atom with a lone pair, or, essentially, ammonia with at least one hydrogen replaced with a carbon (N-R 3 ). Amides consist of a nitrogen atom bonded to a carbonyl group (-NC=O). Nitriles consist of a nitrogen atom triple bonded to a carbon atom. Phenyls: The phenyl group (C 6 H 5 ) is essentially a benzene ring. Phenyls are called aromatic compounds because they alternate between single and double bonds. Phenyl containing compounds include phenol (an alcohol, C 6 H 5 OH), toluene (a substituted methyl group, C 6 H 5 CH 3 ), and aniline (an amine, C 6 H 5 NH 2 ).

ACE Organic Functional Groups

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ORGANIC FUNCTIONAL GROUPS

2011, Academic Competition Enterprises www.acequizbowlcamp.com

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